Category: 101335-11-9

These common heterocyclic compound, 101335-11-9, name is 2-Chloro-4-fluoro-1-iodobenzene, its traditional synthetic route has been very mature, but the traditional synthetic route has various shortcomings, such as complicated route, low yield, poor purity, etc, below Introduce a new synthetic route. Recommanded Product: 101335-11-9

To a solution of 2-chloro-4-fluoro-1 -iodo-benzene (9.0 g, 1 eq.) in DMF (46 ml.) was added cesium carbonate (22.8 g, 2 eq) then 4-chlorophenol (4.5 g, 1 eq.). The mixture was heated at 95 C for 16h. After cooling, an aq. solution of ammonium chloride (230ml_) was added, and extracted 3 times with diethylether. The organic phases were combined and washed successive- lywith an aq. solution of ammonium chloride (2x), aq. solution of NaOH (2%), water, then a saturated aq. solution of sodium chloride. The organic phase was dried and evaporated to give after purification on column chromatography on silica gel, 2-chloro-4-(4-chlorophenoxy)-1 -iodo- benzene as an oil (16,7 g, yield=47%).

The synthetic route of 2-Chloro-4-fluoro-1-iodobenzene has been constantly updated, and we look forward to future research findings.

Electric Literature of 101335-11-9, A common heterocyclic compound, 101335-11-9, name is 2-Chloro-4-fluoro-1-iodobenzene, molecular formula is C6H3ClFI, its traditional synthetic route has been very mature, but the traditional synthetic route has various shortcomings, such as complicated route, low yield, poor purity, etc, below Introduce a new synthetic route.

To a mixture of 8-{[tert-butyl(dimethyl)silyl]oxy}-3-methyl-2-azaspiro[4.5]decan-1 -one (mixtureof isomers) (329 mg, 1.11 mmol) and 2-chloro-4-fluoro-1-iodobenzene (340 mg, 1.33 mmol)in o-xylol (20 ml) was added under an argon atmosphere copper(l) iodide (42.1 mg, 221 pmol), N,N?-imethylethylenediamine (48 p1, 440 pmol) and potassium phosphate (469 mg,2.21 mmol) and the reaction was heated to 1400 for 24 h in a microwave reactor. Upon cooling, the reaction mixture was filtrated through a pad of celite the residue was washedwith ethyl acetate and the filtrate was concentrated under reduced pressure. The crude product was purified by flash chromatography (hexanes/ethyl acetate-gradient, 0% -> 10% ethyl acetate) to give the title compound (280 mg).[C-MS (Method 2): R = 1.75 mm; MS (ESIpos): m/z = 426 [M+H]+ 1H-NMR (400 MHz, DMSO-d6): 6 [ppm] = 7.55 (dd, 1H), 7.44-7.33 (m, 1H), 7.31-7.16 (m,1H), 4.06-3.97 (m, 1H), 3.94-3.85 (m, 1H), 2.12-1.98 (m, 1H), 1.92-1.76 (m, 1H), 1.71 -1 .36(m, 6H), 1.26-1.14(m, 1H), 0.98(d, 3H), 0.88-0.80(m, 9H), 0.01 (d, 6H)

The basis of chemical reaction formula synthesis, the synthesis route is composed of some specific reactions and combined according to certain logical thinking. We look forward to the emergence of more reaction modes in the future.

101335-11-9, name is 2-Chloro-4-fluoro-1-iodobenzene, belongs to iodides-buliding-blocks compound, is considered to be a conventional heterocyclic compound, which is widely used in drug synthesis. The chemical synthesis route is as follows. Formula: C6H3ClFI

7,7-Dimethyl-2-(pyridin-2-yl)-4,5,6,7-tetrahydrooxazolo[4,5-c]pyridine (460 mg, 2.0 m mol), Pd2(dba)3 (92 mg, 0.1 mmol), X-phos (95 mg, 0.2 mmol), 2-chloro-4- fluoro-1-iodobenzene (768 mg, 3.0 mmol), and Na-OtBu (576 mg, 6.0 mmol) were combined in toluene (15 mL) and heated at 1500C by microwave for 3 h. The reaction was evaporated to dryness, diluted with dichloromethane and extracted with water. The combined organic layer was dried using sodium sulfate, filtered, evaporated, and then purified by prep-TLC to obtain the title compound as a yellow solid. (6 mg, 0.87 %). 1H NMR (400 MHz, CDCl3): delta 8.74-8.76 (m, IH), 8.08-8.11 (m, IH), 7.78-7.72 (m, IH), 7.32-7.36 (m, IH), 7.15-7.20 (m, 2H), 6.96-7.01 (m, IH), 4.06 (s, 2H), 3.12 (s, 2H), 1.46(s, 6H); LC/MS: m/e = 358 (M+H)+.

The synthetic route of 101335-11-9 has been constantly updated, and we look forward to future research findings.

Related Products of 101335-11-9, Each compound has different characteristics, and only by selecting the characteristics of the compound suitable for a specific situation can the compound be applied on a large scale. 101335-11-9, name is 2-Chloro-4-fluoro-1-iodobenzene, This compound has unique chemical properties. The synthetic route is as follows.

To a mixture of (Z)-4-(l-(l-(tetrahydro-2H-pyran-2-yl)-lH-indazol-5-yl)-2-(4,4,5,5- tetramethyl-l,3,2-dioxaborolan-2-yl)but-l-en-l-yl)benzaldehyde IV, 1.2 equivalents of 2- chloro-4-fluoro-l-iodobenzene, 1.0 mol% palladium acetate (CAS Reg. No. 003375-31-3) and 2.7 mol% triphenylphosphine (CAS 000603-35-0) in THF is added 5.0 equivalents of 15 %-w/w aqueous NaOH at 67 C. The reaction mixture stirred at 67 C for 8 – 12 h. Upon desired conversion, the phases were allowed to settle and the aqueous layer was separated. The organic phase was diluted with toluene and washed with 5% aqueous NaOH followed by water. The organic phase so obtained was concentrated at atmospheric pressure to a desired volume, and then cooled to ambient temperature to give toluene solution (E)-4-(2-(2-chloro- 4-fluorophenyl)-l-(l-(tetrahydro-2H-pyran-2-yl)-lH-indazol-5-yl)but-l-en-l- yl)benzaldehyde III. 1H NMR (300 MHz, DMSO-d6): delta 9.82 (s, 1H), 8.15 (s, 1H), 7.78-7.71 (m, 2H), 7.61 (d, 2H), 7.43-7.27 (m, 3H), 7.15 (m, 3H), 5.86 (dd, 1H), 3.93-3.85 (m, 1H), 3.79-3.68 (m, 1H), 2.44-2.36 (m, 3H), 2.10-1.96 (m, 2H), 1.81-1.67 (m, 1H), 1.63-1.53 (m, 2H), 0.92 (t, 3H); LCMS: 405 [(M-THP+H)+H]+.

The chemical industry reduces the impact on the environment during synthesis 2-Chloro-4-fluoro-1-iodobenzene. I believe this compound will play a more active role in future production and life.

Reference:
Patent; F. HOFFMANN-LA ROCHE AG; GENENTECH, INC.; BACHMANN, Stephan; FANTASIA, Serena Maria; GOSSELIN, Francis; HAN, Chong; HILDBRAND, Stefan; HUMPHRIES, Theresa; JENNY, Christian; LIM, Ngiap-Kie; MCCLORY, Andrew; MOESSNER, Christian; REGE, Pankaj D.; SAVAGE, Scott; ZHANG, Haiming; (66 pag.)WO2017/60326; (2017); A1;,
Iodide – Wikipedia,
Iodide – an overview | ScienceDirect Topics – ScienceDirect.com

Synthetic Route of 101335-11-9, A common heterocyclic compound, 101335-11-9, name is 2-Chloro-4-fluoro-1-iodobenzene, molecular formula is C6H3ClFI, its traditional synthetic route has been very mature, but the traditional synthetic route has various shortcomings, such as complicated route, low yield, poor purity, etc, below Introduce a new synthetic route.

Intermediate XI A solution of isopropyl magnesium chloride (100 mL, 2.0M in Ethyl Ether) was added to a solution of 2-chloro-4-fluoro-1-iodobenzene (25 g, 97.5 mmol) in 300 mL THF chilled in an ice bath. The solution was then stirred at RT overnight. The solution was chilled in a CO2/acetone bath and trimethyl borate was added (23 mL, 200 mmol). The solution was warmed to RT and stirred for 6 h. The suspension was partitioned between water and ethyl ether (emulsion). The phases were separated and the organic phase concentrated. The residue was treated with 200 mL 2N HCl and stirred overnight. The suspension was then extracted with ethyl ether (2*) and the combined organics washed with brine, dried over MgSO4, filtered and concentrated to give 13.3 g solid. The crude solid was suspended in hexanes, filtered and washed 2* (hexanes) to give 2-chloro-4-fluoro-phenylboronic acid. LC 1: 1.65 min.

The synthetic route of 101335-11-9 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; Doherty, James B.; Stelmach, John E.; Chen, Meng-Hsin; Liu, Luping; Hunt, Julianne A.; Ruzck, Rowena D.; Goulet, Joung L.; Wisnoski, David D.; Natarajan, Swaminathan Ravi; Rupprecht, Kathleen M.; Bao, Jianming; Miao, Shouwu; Hong, Xingfang; Sinclair, Peter J.; Kallashi, Florida; US2003/92712; (2003); A1;,
Iodide – Wikipedia,
Iodide – an overview | ScienceDirect Topics – ScienceDirect.com

In the chemical reaction process, reaction time, type of solvent, can easily affect the result of the reaction, thereby determining the yield and properties of the reaction product. An updated downstream synthesis route of 101335-11-9 as follows. Formula: C6H3ClFI

Step 1. Ethyl 2-(4-(2-chloro-4-fluorophenyl)-4-hydroxycyclohexyl)acetate. A solution of n-butyllithium in hexanes (1.6 M, 81.4 mL, 130 mmol) was added dropwise to a solution of 2- chloro-4-fluoro-l-iodobenzene (16.6 mL, 130 mmol) in tetrahydrofuran (197 mL) at -78C. The reaction mixture was allowed to stir at -78C for 1 h before the addition of ethyl 2-(4- oxocyclohexyl)acetate (19.2 mL, 109 mmol) in one portion. The reaction was allowed to warm to room temperature and stirred at room temperature for 1 h. The reaction was quenched with a saturated solution of ammonium chloride (500 mL) and extracted with EtOAc (3 x 150 mL), combined organics dried (Na2S04) and concentrated under reduced pressure. The residue was purified by flash chromatography on silica, eluting with 0-40% EtOAc in hexanes to yield the product as a colorless oil (26.7 g, 78%). 1H NMR (400 MHz, CDCb) d 7.65 (dd, / = 8.86, 6.30 Hz, 1H), 7.21 – 7.09 (m, 1H), 7.03 – 6.94 (m, 1H), 4.27 – 4.07 (m, 5H), 2.62 – 2.47 (m, 2H), 2.46 – 2.18 (m, 10H), 2.15 – 1.82 (m, 6H), 1.78 – 1.34 (m, 7H), 1.34 – 1.22 (m, 7H). [M-H2O+H] = 283.1.

According to the analysis of related databases, 101335-11-9, the application of this compound in the production field has become more and more popular.

Reference:
Patent; DART NEUROSCIENCE, LLC; BASINGER, THOMPSON, Jillian; BOOKSER, Brett; BURLEY, Scott; GARCIA-REYNAGA, Pablo; HUDSON, Andrew; PETERS, Marco; PRATT, Benjamin; THOMPSON, Aaron; TRAN, Joe; VALDEZ, Lino; (211 pag.)WO2019/168866; (2019); A1;,
Iodide – Wikipedia,
Iodide – an overview | ScienceDirect Topics – ScienceDirect.com

Each compound has different characteristics, and only by selecting the characteristics of the compound suitable for a specific situation can the compound be applied on a large scale. 101335-11-9, name is 2-Chloro-4-fluoro-1-iodobenzene, This compound has unique chemical properties. The synthetic route is as follows., Formula: C6H3ClFI

INT 18 2-Chloro-6-fluoro-3-iodobenzonitrile Step A: 2-Chloro-6-fluoro-3-iodobenzaldehyde A solution of diisopropylamine (870 mg, 8.6 mmol) in anhydrous THF was added n-butyllithium (2.5 M in hexanes, 3.1 mL, 7.8 mmol) dropwise over 5 min under nitrogen at 0 C. After 10 min, the reaction mixture was cooled to -78 C and 2-chloro-4-fluoro-l-iodobenzene (2.0 g, 7.8 mmol) was added dropwise over 5 min. After 1 h at – 78 C, DMF (640 mg, 8.6 mmol) was added dropwise over 5 min. After a further 10 min at -78 C, the reaction mixture was quenched by the rapid addition of acetic acid (2.0 mL), followed quickly by water (50 mL). The cold solution was extracted with diethyl ether and the organic extracts were washed with diluted HCl (0.2 M, 25 mL), water, brine and dried over anhydrous sodium sulfate. The solvent was removed under reduce pressure and the resulting residue was then purified by silica gel chromatography to provide 2-chloro-6-fluoro-3-iodobenzaldehyde. 1HNMR (400 MHz, CDC13) delta 10.34 (s, 1H), 8.04 (m, 1H), 6.92 (dd, J = 9.4, 9.4 Hz, 1H).

Chemical properties determine the actual use. Each compound has specific chemical properties and uses. We look forward to more synthetic routes in the future to expand reaction routes of 101335-11-9.

Reference:
Patent; MERCK SHARP & DOHME CORP.; WALSH, Shawn; PASTERNAK, Alexander; CATO, Brian; FINKE, Paul, E.; FRIE, Jessica; FU, Qinghong; KIM, Dooseop; PIO, Barbara; SHAHRIPOUR, Aurash; SHI, Zhi-Cai; TANG, Haifeng; WO2013/39802; (2013); A1;,
Iodide – Wikipedia,
Iodide – an overview | ScienceDirect Topics – ScienceDirect.com

Electric Literature of 101335-11-9, These common heterocyclic compound, 101335-11-9, name is 2-Chloro-4-fluoro-1-iodobenzene, its traditional synthetic route has been very mature, but the traditional synthetic route has various shortcomings, such as complicated route, low yield, poor purity, etc, below Introduce a new synthetic route.

10180] To a stirred solution of 208 (1.8 mmol) in 2-methyl THF (30 mE), iodobenzene (209, 1.8 mmol), 4M aqueous KOR (S mE) and Pd(PPh3)2C12 (63 mg, 0.09 mmol) were added and the mixture was degassed with nitrogen for 15 mm and heated at 80-90 C. for 8-12 h. Upon completion, the reaction mixture was diluted with EtOAc. Organic layer was washed with water followed by brine, dried over anhydrous sodium sulphate, filtered and concentrated. The crude product was purified by silica gel chromatography (2:8 EtOAc in n-hexane) to give a desired product (211, 0.74 mmol, 41%):_10576] The reaction was carried out according to Scheme i, Step-S using tert-butyl ((E)-4-(dimethylamino)-4-oxobut- 2-en-i -yl)(2-((5-((E)-4,4,4-trifluoro- i -(3-fluoro-i -(tetrahydro-2H-pyran-2-yl)- i H-indazol-5-yl)-2-(4,4,5,5-tetram- ethyl-i ,3,2-dioxaborolan-2-yl)but- i-en-i -yl)pyridin-2-yl) oxy)ethyl)carbamate (i.2 g, i.49 mmol) for compound 208 in 2-m and 2-chloro-4-fluoro-i-iodobenzene (0.383 g, i.49 mmol) for compound 209. Reaction mixture was stirred at 80 C. for 8 h. The crude material was purified by combiflashusing 3% MeOR in dichloromethane to afford the title compound of Ex. 59 Step-S (0.92 g, 76%).

The synthetic route of 101335-11-9 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; Eisai R&D Management Co., Ltd.; BOCK, Mark; HAO, Ming-Hong; KORPAL, Manav; NYAVANANDI, Vijay Kumar; PUYANG, Xiaoling; SAMAJDAR, Susanta; SMITH, Peter Gerard; WANG, John; ZHENG, Guo Zhu; ZHU, Ping; (141 pag.)US2016/347717; (2016); A1;,
Iodide – Wikipedia,
Iodide – an overview | ScienceDirect Topics – ScienceDirect.com

Each compound has different characteristics, and only by selecting the characteristics of the compound suitable for a specific situation can the compound be applied on a large scale. 101335-11-9, name is 2-Chloro-4-fluoro-1-iodobenzene, This compound has unique chemical properties. The synthetic route is as follows., HPLC of Formula: C6H3ClFI

Preparation 9 IB: (2-Chloro-4-fluorophenyl)(3-fluoro-4-(pyrimidin-5-yl)pyridin-2- yl)methanoneTo a solution of 2-chloro-4-fluoro-l-iodobenzene (0.307 g, 1.199 mmol) in THF (Volume: 1.622 ml) cooled to -10 C was added isopropylmagnesium chloride, 2M in THF (0.699 ml, 1.399 mmol) in one portion. After 30 min, 3-fluoro-4-(pyrimidin-5- yl)picolinonitrile (0.200 g, 0.999 mmol) was added. The reaction mixture was stirred at -10 C for 30 min, then allowed to warm to room temperature and stirred overnight. Water and ice were carefully added, followed by acidification with 6 M HC1. After stirring for 1 hr, CH2C12 was added and the pH was adjusted to 8.5 with aqueous 4 M NaOH. The layers were separated. The aqueous phase was extracted with CH2CI2 (5X). Organics combined, dried over Na2S04, filtered, and concentrated to afford an orange residue. The crude material was dissolved in a minimal amount of CH2CI2 to be chromatographed. Purification of the crude material by silica gel chromatography using an ISCO machine (24 g column, 35 mL/min, 60-100% EtOAc in hexanes over 23 min, tr = 9 min) gave the title compound (0.029 g, 0.074 mmol, 7.44% yield) as an orange solid.

According to the analysis of related databases, 101335-11-9, the application of this compound in the production field has become more and more popular.

Reference:
Patent; BRISTOL-MYERS SQUIBB COMPANY; BALOG, James Aaron; HUANG, Audris; VELAPARTHI, Upender; LIU, Peiying; WO2013/49263; (2013); A1;,
Iodide – Wikipedia,
Iodide – an overview | ScienceDirect Topics – ScienceDirect.com

Reference of 101335-11-9, The chemical industry reduces the impact on the environment during synthesis 101335-11-9, name is 2-Chloro-4-fluoro-1-iodobenzene, I believe this compound will play a more active role in future production and life.

Sodium methanethiolate (5g) was added to a solution of 4-fluoro-2-chloro-iodobenzene (18.3g) and stirred for 20h. The mixture was poured into water, extracted with ether, washed with brine, dried (MgS04) and evaporated. Yield 18. 5g. 1H NMR DMSO-d6: 8 7.81 (d, 1H), 7.43 (dd, 1H), 6.98 (dd, 1H), 3.32 (s, 3H)

In the field of chemistry, the synthetic routes of compounds are constantly being developed and updated. I will also mention this compound in other articles, 2-Chloro-4-fluoro-1-iodobenzene, other downstream synthetic routes, hurry up and to see.

Reference:
Patent; ASTRAZENECA AB; WO2004/89885; (2004); A1;,
Iodide – Wikipedia,
Iodide – an overview | ScienceDirect Topics – ScienceDirect.com